Being Irrational, Illogical, and Dreamy: A Leader’s Guide to Dreaming Big

by | Aug 12, 2020

The Beatles’ “Yesterday,” revered by many as the best song of the 20th century, was written by Paul McCartney in 1964. Yesterday

As legend has it, the melody to “Yesterday” came to Paul McCartney in a dream. When he woke up, he scurried to a piano. “I just fell out of bed, found out what key I had dreamed it in…and I played it.”

And so, one of the greatest songs ever written simply came to its composer… in a dream. 

As it turns out, this was an especially lucrative dream, as Yesterday is estimated to have amassed over $20m in royalties since it was released. Not bad for a night’s work!

It is an amazing story, and not the only account of incredible ideas, revelations, and inspiration that have been conceived in the wee hours in the dark corners of the unconscious mind.  

Salvadore Dali’s Persistence of Memory, which put him on the map in the 1930s, was said to be inspired by a lucid dream he had. His dream, he later said, was surreal (pun intended).

Niels Bohr, the OG of quantum mechanics, credits his early 20th-century discovery of the structure of the atom to an especially lucid dream. At the time, his theories of the structure of an atom were dead-ended —he ran into the scientists equivalent of writer’s block— until one night he went to sleep and began dreaming about atoms. He saw the nucleus of the atom, with electrons spinning around it, much as planets spin around their sun.

Thank heavens for Bohrs’ dream. Without it, we might still be bumbling around thinking that matter is made up of tiny Skittles like a bunch of dufuses. 

And without inspiration from his own especially inspiring dream involving a weird naked Indian, Wayne Campbell and sidekick Garth Algar would have never come to discover Waynestock. Party on, Wayne! 

You get the point. Dreams are a fascinating – and important – phenomenon. And we all have them. Lots of them. It’s estimated that by the age of 60 most of us will have dreamed 197,100 dreams over 87,000 hours.

Much has been studied about dreams (known as Oneirology), and yet, still so little is known. Oneirologists have long disagreed on the purpose that dreams serve. Are they strictly random brain impulses, or are our brains actually working through issues from our daily life while we sleep — as a sort of coping mechanism? Do they serve an important evolutionary purpose? 

But many preeminent dream researchers—dream nerds, as they call themselves—do agree that people should take the time to interpret their dreams, as we have a great deal to learn from them. We won’t cover that here. But there’s some fascinating and relevant research on using dreams as practice to improve performance in real-life scenarios, and the power of ‘dream therapy’ as a way to help leaders understand and release the pressure of working life

But let’s bring this back down to earth. Using a more liberal definition of the idea of “dreaming,” it is widely cited that the most game-changing leaders among us are prolific “dreamers.” 

Martin Luther King was a dreamer. He said so himself. 

Steve Jobs was a dreamer. A retail executive who was once tasked with revitalizing the Disney Store called Steve Jobs, Disney’s largest shareholder, to ask for advice. Jobs said, “Dream bigger.”

Well-known thought leader and entrepreneur Brian Tracey, said it well:

“All successful people —men and women— are big dreamers. They imagine what their future could be, ideal in every respect, and then they work every day toward their distant vision, that goal or purpose.”


Great leaders are big dreamers. Small visions don’t move mountains. They don’t transform companies, careers, lives. They don’t have the power to change the world. 

Big dreams do.

And the thing about big dreams is that dreaming big is actually better… and in many ways, easier. See, when you’re trying to go 10% bigger (the “Incrementalist’s Trap,” as I call it), you will be competing with everyone else trying to go 10% bigger. But when you think 10x bigger, it forces you to think differently so that you’re not playing the same game everyone else is. It can inspire an amazing group of people to come by your side. 

The question is: is going 10x bigger really 100x harder than going 10% bigger? Does it require 100x the resources? 100x the computing power? 100x the brain cells?

In most cases, absolutely not. 

Did MLK’s dream require 100x the money, resources, brainpower? Negative. (More than anything, it needed courage.) 

Unrealistic things might be easier to accomplish than you think because when it comes to goals that are “good enough“, the competition is fierce. Only when you dare to dream big does the competition thin out considerably. 

Thomas Edison didn’t aspire to merely improve the candle. Rosa Parks was not just claiming a seat on a Montgomery, Alabama bus. Virgin Galactic founder and CEO Sir Richard Branson is not seeking to just build a faster passenger aircraft.



JFK was a dreamer. His speech at Rice University compelled a nation to rally behind a crazy, but inspiring dream—landing a man on the moon by the end of the decade. We may forget that in the early 1960’s, this dream seemed outlandishly crazy. It was… well… big. 

But unlike the JFK example, we shouldn’t have to wait for a war to dream big. 

New flash: Life is microscopically short. You could die today. You could go tomorrow.  In twenty minutes or twenty years. Confronting our precious impermanence is scary, but should fill us with a sense of purpose and urgency to get out there and pursue a big, hairy, audacious dream. Now. 

The Stoic philosophers talked a lot about this idea. They called it Memento Mori. By confronting our mortality, they believed that human beings would be primed to live a more full life. And dream bigger. 

“Suppose that a god announced that you were going to die tomorrow “or the day after.” Unless you were a complete coward you wouldn’t kick up a fuss about which day it was—what difference could it make? Now recognize that the difference between years from now and tomorrow is just as small.”  ~Marcus Aurelius

As leaders, dreaming is all about identifying a gigantic problem or opportunity in your company, in your customers’ lives, or in the world. It is about giving a damn about this problem or opportunity. It is about taking a stand for changing the paradigm, for creating a better company, and better world. It has to have heart. 

It is about envisioning a bold and even science-fiction-like solution to that problem. And envisioning a future that is far brighter than the present once that solution is brought into existence. 

It is about enrolling a committed and passionate group of people into your dream. People who aspire to do big things need people by their side. Find people. Awaken in them the same sense of longing for this better future. Connect your dream to what matters to them already. Enroll them by creating with them a shared vision for what’s possible. 

Then create the context and environment where people can be weird and radical—and safe—in pursuing that dream. Dreamers create environments that are dreamy. They tell their teams, “You can do it. You can go 10x bigger, and change the world that much. I expect huge change from you, not just incremental change.” 

Not sure where to look for your dream? 

Well, the thing that you are up against in the world can be the place to look for your dream. 

For example, if you are up against the challenges of being a rising woman leader in a male-dominated company or industry, your dream might be to help create gender equality in the workplace. It is close to home for you. It has real emotional resonance with you.  If you are emotionally connected to the cause, you’ll be much more strongly invested in it. 

As a business leader, big dreams take root in the biggest and hairiest choke-points in your industry or in your customers’ lives. Start by asking yourself and your customers: “What is the one thing that I hate most about my industry? What is driving me nuts? What is the one structural factor that everyone in our industry would agree is a pain in the ass, but has been accepted as “just the way it is” nonetheless.”

Uber is a prime example. Before Uber, the taxicab industry was rife with things that drove consumers nuts. Price opaqueness. An often unpleasant customer experience… with little or no accountability on the part of drivers. And vehicles that often smelled like old pastrami sandwiches. But consumers had long accepted these unpleasantries as “just the way that it is.” Until Uber came along with a dream. 


Push off your goals and dreams no more. Get started. 

“But that’s easier said than done,” you may be thinking. 

What’s stopping you from going for it? Why haven’t you gone for it yet? You’ve got a lot of reasons surely. Its too hard. It might not work, and I might fail. Its too expensive. People will judge me. Everyone’s saying I shouldn’t.

At this point, you might be finding yourself having a conversation with yourself. On one side of the dialogue is you. Like, the real you. On the other side is the little invisible voice inside of your head who is like a really negative, gruff, and ornery houseguest who has overstayed his/her welcome. S/he tries to keep you small. You have tried kicking him to the curb, only to hear a knock on our door hours later… he’s back… unkempt as ever with a six pack of sabotage in his hand.

Cohabitating with this bad houseguest can destroy dreams. It can create insecurity, self-imposed limitation that can create a huge barrier to boldly venturing into the direction of your dreams. How do we send our annoying houseguest on a one-way trip to Getouttamyway’ville without a cell phone?

Find and examine the beliefs that are holding you back. What is your bad houseguest saying to you? What pessimistic thoughts reoccur in my head every time I think about about this dream? What self-defeating stories have I created based on my past failures with important goals, or my past failing in leadership situations? How do these limit me? How are they creating barriers to getting started?

Overcoming limiting beliefs requires that we replace each of them with new and more empowering ways of thinking. Your challenge is to create new pieces of self-talk, perspective, life philosophies, or slogans that really resonate with you on an experiential level, are believable, and you can really lean into. 

But what about the risk of failure? After all, the bigger the dream, then it is rational to expect the higher the risk that things don’t work out. 

Take the time to define your nightmare. Write out all the doubts, fears, and “what-ifs.” What will go wrong if this doesn’t work out? Actually write it down, and dump it all onto a page, and let the words stare at you. This allows you to bring all of your nebulous, previously undefined fears into light.

Visualize, in vivid detail, this worst-case scenario until it feels like the nightmare has leapt off the paper and transpired.

Ask yourself: “If this happened, would that be the end of me? Could I come back from it? How likely is that to even happen?”

Finally, ask yourself: “What do I fear more… that nightmare scenario… or dying and never knowing what that dream could feel like?”

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